Choosing Sides
by MerrytheAngel
Summary: Dean was well-known for his crimes. Now that he'd been caught, he's sent to the toughest prison in the United States. Normally, he'd escape before the night was up, but something kept him here - his cellmate. Prison!AU Normal!AU SLASH Destiel, Sabriel, maybe others :D
1. Chapter 1

Footsteps reverberated off of the cold walls as Dean Winchester was led to his cell. This prison, his new home, was the biggest in Kansas. It housed some of the biggest and meanest criminals in the country. Dean now joined these ranks.

Police departments and various federal governments had been on the hunt for him for years. He had eluded them in many creative ways, including a smoke bomb and identity theft. Even when he had been caught, he always escaped. No handcuffs could hold him. Perhaps that is why he was in iron bars, specifically placed so that he had little movement.

Dean hummed contentedly as they stomped closer to his cell. He couldn't help but wonder in what way he should escape this time. This wouldn't be the first time he had already gone through the entire process of prison. He just never stayed for bedtime - always dinner, though.

When they reached his cell, Dean saw another prisoner already there. How interesting… he'd never had a cellmate before. They always kept him by himself. This man was big, but far from mean-looking. The guy was taller than Dean, probably 6'4", and had shaggy brown hair that hung down in his eyes, which were a bright hazel.

The prison guard unlocked Dean from his cuffs and shoved him inside the cell. "No funny stuff, Winchester. We'll be back for you two at supper time." And the guard left. No goodbyes, how rude, Dean thought before turning to his new friend.

"Hello." The kid said, giving Dean a smile. Strange, no one had addressed him like that since he had become one of the top most wanted. Does this kid even know who he is? "I'm Sam – Sam Campbell." He stuck his hand out politely. Dean just stared at him.

"Dean Winchester." He replied, not bothering to shake Sam's hand. He looked out through the bars to the other cells. Where were the other prisoners?

"Everyone else is out in the courtyard." Sam told him. His voice was quiet, but held a force behind it that beckoned attention. How is this kid expected to survive prison when he was so gentle?

"Why are you locked inside, then?" Dean asked, deciding to tread carefully. Sam could be a mass murderer for all he knew. After all, who was he to judge someone's appearance? Maybe Sam kills with kindness. Dean almost chuckled at that, but instead turned back to Sam solemnly.

Sam was looking down at his feet. "I got in a fight." He looked like a freaking school kid; a giant one, of course. "One of the other guys came over and started pushing me. I pushed back, and a guard saw."

Dean studied Sam. He could tell the boy was uncomfortable. Geez, how long could he have been in here? Surely not long, he was far too timid to have survived too long in this joint. Dean almost asked him how long he'd been in the joint, but Sam asked a question himself.

"Why are you in here, Mr. Winchester?" Now Sam really looked like a freaking kid. Gosh, those puppy-dog eyes would kill anyone. This kid has to have some dark, badass secret, right?

"You really don't know who I am? I've been all over the news for the last year!" Dean asked, surprised that anyone would not know him. If you were to walk up to someone in the middle of the street and ask if they knew who Dean Winchester was, they'd tell you that they damn right do.

Sam sat on the edge of the bottom bunk and stared at his hands. "I've heard the others talk about you, just a few times, but we don't have access to a television.

Dean couldn't believe it - the kid didn't know who he was! He sighed deeply; it doesn't matter. He won't have to deal with this kid for too long. Who cares if there is one person out there who doesn't know who he is and what he's done?

"You know what?" Dean said, walking over to clap his cellmate on the back, surprising Sam. "It doesn't matter. All I want and need is a nice beer and a slice of pie." Ah, pie, Dean's favorite thing in the world.

Sam looked as though he was about to say something, but was interrupted by one of the guards. This guard was not the same one who had brought Dean in. This guard was a female.

"Time for supper, you two." She said, giving Sam a smile, which he returned. Dean followed Sam as he stepped out of the cell. The woman stopped him with a slim hand to his chest. She then took handcuffs out from behind her.

"What?" Dean snapped, mockingly, "You're going to cuff me, but not him?" That didn't seem very fair to Dean.

The guard shrugged, giving a smirk. "I know Sam, Winchester. I trust him to not escape." She knows him? That means either they've had history or Sam has been in here longer than Dean had originally thought.

The cafeteria was huge compared to the prisons Dean had occupied before. Tables lined the walls and the center of the room, but left plenty of space for the prisoners to wander about. The food lines were long and growing by the time Dean and Sam had made it from their cell.

"Wow, this is pretty nice, I might actually want to stay the night this time." Dean remarked, looking about and giving smirks to wandering eyes. Some people knew who he was, and for that he was glad.

"Sammy!" A chipper voice rang out from behind the two. Dean turned to find a blond-haired, golden eyed man who was shorter than he was waltzing up to them. He wrapped an arm around Sam's shoulder, smiling widely. "I see you're still doing well, even after your incident with Luci."

Sam chuckled, blushing. "Yeah, I'm fine, Gabe." He motioned an arm towards Dean. "This is Dean Winchester, my new cellmate."

The man's smile faltered some as he studied Dean. "I know who he is." He stated, releasing Sam and walking right up to Dean. "If you cause my buddy Sammy here any trouble, it'll be your head on a platter."

Dean raised an eyebrow at the short man. Was he supposed to be intimidating? Dean didn't know whether he should laugh or not, so he shrugged it off, and gave the man his most charming smile.

"And who do I have the pleasure of being threatened by?" Dean asked.

Shorty returned Dean's smile, but warning shone in his eyes. "Gabriel Milton."

Dean nodded in recognition. Even he had to give credit where it was due; this man was a big deal. "You're the one who committed the Old Tale murders. Man, I gotta admit, the whole Gator in the Sewers trick was hilarious."

Gabriel's smile widened at the praise. "That's everyone's favorite."

Sam hummed from next to Gabriel, catching the man's attention. "Well, everyone's favorite but Sammy's." Gabriel winked at the taller man. "Sammy doesn't really like the bloodshed - even though every person I killed deserved it."

This was interesting, Dean thought. Sam doesn't like bloodshed? There weren't many in this prison convicted for less than murder, so why was this boy in here? Maybe he was framed or an accident that the police chose to cover up? Many different possibilities ran through the Winchester's mind, all focused on Sam.

Sam rubbed the back of his head sheepishly. He looked around, as if the people were staring at him. Gabriel then wrapped an arm around Sam's waist, and Sam wrapped an arm around his shoulders. Dean raised an eyebrow to this. They were together? That didn't bother Dean, of course. He wasn't judgmental, especially to people who found themselves in prison.

"Why don't we, uh, find a place to sit, huh?" Sam asked, motioning to the closest empty table with his head. His eyes kept darting around nervously, Dean noticed. Something made him skittish real quickly. Dean tried to see what, but Gabriel's voice broke his thoughts.

"Great idea, kiddo. You go on ahead, Dean-o and I will meet you over there." Sam gave him a questioning look, but slowly made his way over. Gabriel gave his arm a gentle pat. "Don't worry, I got my eyes open."

Dean looked between the two, trying to decipher what exactly was going on. Gabriel then turned to Dean and said, "Let's step over here and chat for a mo, eh?" Dean followed, not saying a word.

They went to stand over by the doors that Dean and Sam entered to get in here, Gabriel's eyes constantly darting everywhere. "Okay, I'm going to tell you the full deal with this place - that is, first, if you are staying." Gabriel focused his eyes on Dean, asking a question.

Dean had to admit, though this place would not be impossible to escape, it would be difficult. He was also quite curious to the back-story of Sam Campbell. Perhaps it wouldn't wreck his rep too much to stay at least a night or two. "Yeah, I'll stick around for a bit. Something tells me this place is more than just big walls and pro-killers."

Gabriel chuckled, removing his bright eyes from Dean's. It was strange. Just standing around and talking to this man, who one would never assume to be a murderer. With Dean, everyone was always edgy and suspicious, but Gabriel was the friendly sort, with a big smile and enticing, golden eyes. He was all smiles, laughs, and a brain full of creative ways to kill.

"You could say that," Gabriel said, still looking around. He then turned to Dean, smile flattened, his face serious. "But we need to talk first. This place is a web of secrets and sides. Your best chance at survival is to keep your secrets, choose your side wisely, and don't get caught with the enemy."

Dean scoffed. "This is just a prison. I know prisons have their gangs or whatever, but this is starting to sound -"

"This is the way you last in here." Gabriel looked at him, complete and utterly serious. A darkness shone in his eyes - Dean's first sighting of the murderer. "Even if you were to try to escape, you would never make it. This ain't no ordinary prison, Winchester. If you're willing to listen, I have a plan, but this means you're on my side."

Dean thought carefully, looked around at all the other faces, wondering what their "side" was. He then saw Sam, and knew he must be on Gabriel's side. He sighed, and gave Gabriel a smile. "Let's hear it, Trickster."


	2. Chapter 2

"So, there are three different groups in this joint. Lucifer's, Michael's, and Castiel's." Gabriel explained, eyes moving about constantly, keeping watch. "We, my friend, are a part of Castiel's group. Technically, we are the renegade group. The reason we exist is because we are sick of Mike and Luci's crap."

Gabriel spoke of the two group leaders as though he really knew them; although, that could just be how Gabriel spoke of people. "Michael and Lucifer have been in this prison a long time – longer than most others. The only exception is myself." He smirked, as though having been locked away for so long was an honor.

Dean had to satisfy his curiosity, so he asked, "How long has Sam been here?"

Gabriel's face went solemn at the mention of Sam. "Not long," he answered quietly. "but he's caught a lot of attention."

"What did he do to get in here?" Dean glanced over at the boy, who was chatting with another inmate, but kept looking over at them.

"According to the guards' story – he set his girlfriend and their house on fire. According to him – he was framed and forced to watch his girlfriend die right in front of him."

Dean winced. No wonder the kid looked so out of place and behaved so much differently than the others; he wasn't even a murderer. He studied Gabriel's face. He looked so sympathetic for Sam – he really cared for him. Dean hadn't even known that it was possible to be in a functioning relationship while in a prison.

"What sort of attention has he got?" Dean asked, remembering Gabriel's statement from before.

Gabriel hesitated before answering. This looked as though it would delve into tricky territory. "It was Lucifer. He set his sights on Sam the moment he arrived. The poor kid was a mess, and he didn't know or trust anyone, of course."

He looked around nervously, as though looking for Lucifer (which Dean now realized, he probably was). "I was on Lucifer's side at the time. I didn't want to be, but I was – I was sort of with – "

"You were in a relationship with Lucifer." Dean stated for him. Gabriel nodded, then shrugged.

"Kind of – you couldn't really call it a relationship. More of a sexual release." Gabriel shifted around, uncomfortably. "Lucifer isn't the gentlest person. He cornered Sam, terrified him with sweet words and unnecessary touches. I was sickened to think that I had been just like Sam, the recipient of Lucifer's advances. I just wanted to protect him."

Dean nodded, seeing where this was going. "You broke it off with Lucifer to be with Sam, then you ran to this other guy, Castiel."

Gabriel gave a small smile. "Cas was completely understanding, and stood ready to back us at any moment. Could have used him earlier, actually. Lucifer got a little pushy with Sam, and when Sam stood his ground, they both got hauled off."

"I see, and then that's where I came in." Dean concluded, interests perked at having all of the story. Well, Dean was certain it wasn't entirely complete, but he had what he needed to know.

"Yep, now you're all caught up." Gabriel agreed, clapping Dean on the shoulder and leading him back to the table where Sam waited. "So, all you need to do is keep your head down and make it clear whose side you're on."

"Where is this Castiel?" Dean asked.

Gabriel pointed to the corner of the room, where a small group of people stood. "Tall guy, black hair." The guy was shorter and leaner than Dean, but he looked strong. He couldn't tell much more from his distance. He was standing with a blond man who wore an expression similar to the one Gabriel always wore, and a woman with black hair who was very obviously flirting with Castiel.

"Good to know." Dean replied, sitting down at the table with Sam and the man he was talking to. Gabriel followed suit, sitting right next to Sam, and Dean saw his hand slide over so it rested on Sam's thigh. The boy seemed to visibly relax.

"Hello, gentlemen." The unknown man greeted with a rather smug smile. Dean instantly didn't like him. "Gabriel," he nodded, then settled his gaze on Dean. "I don't believe we've met." He held his hand out. "Crowley."

Creepy man with knowing, intelligent eyes that will only give one name – definitely creepy. Dean was almost certain that the man probably knew who he was. He decided to test his theory – his gut was rarely wrong.

Without taking Crowley's hand, Dean answered, "Dean Winchester, but I have a feeling you knew that." Crowley only smiled, the tilted his head at Dean in agreement. He then clapped his hands and stood from the table, gaze resting on Sam. "Well, Moose, it was delightful talking with you, as usual."

He left, and Sam didn't look the least bit happy. "He makes me uncomfortable." The kid admitted, eyes wide and honest.

Gabriel chuckled and Dean asked, "What side is he on?"

Gabriel raise an eyebrow. "Crowley? God only knows. I think he's on our side, but you can never tell with him. Don't worry about it, Crowley is a crooked, egotistical asshole, but he's not much for lying. He just might not tell you the whole truth."

Dean nodded in understanding. He studied Sam, who was still looking around anxiously, but not at all as strung up as he had been as before, when he was sitting alone. The kid looked like a broken vase that had been put back together with duct tape. He was holding on, but he was extremely stressed out. This open environment has him as wired at a guitar.

A whistle blew, and all of the inmates stood and scrambled about to leave. Suppertime was over. It was time to prepare for bed. With so many prisoners, everyone had to get ready early, so everyone would be ready for bed when it was time for lights out.

Dean, Gabriel, and Sam all stood as well, and made for the door they had come from. They had made it about halfway to the bathrooms when a guard stopped them. "I don't think so, Milton. You're on the other side of this block. Go around the way you're supposed to."

Gabriel glared at the guard. His cell was in the same block as Sam and Dean's, but he was on the other side of it, and was supposed to get there through the other doors, not through the bathroom. This must be a common issue if the guard knew exactly where to stop them at.

At one final demand from the guard, Gabriel turned to Sam, gave him a hug and kiss on the cheek. Dean looked away to give them some privacy, unlike the guard, who just stared like he had seen this same scene play out a dozen times.

"Hey, what's your problem?" Dean barked out, angered at the guard's inconsiderate behavior. "Can't you see these guys need a moment? The least you could do is look away!"

"Dean, it's not a big deal." Gabriel said gently. The guard looked annoyed, but didn't say anything to Dean. He just moved forward to push Gabriel along. The blond walked away, but turned mid step to wink at Dean and blow a kiss to Sam.

Dean turned to Sam, but didn't say a word at the look on his face. He was smiling shyly, a blush spread across his face. He wasn't sure if it was from Gabriel or the fact that Dean stepped in and scolded the guard.

After the two cleaned up, made it back to their cell, and had settled into their beds, Dean heard Sam say quietly from his bunk, "Thank you, Dean."

Dean didn't reply.


End file.
